Surfactant, and toiletry or detergent composition containing the same

ABSTRACT

Provided is a novel surfactant which is less irritating to the skin or the mucous membrane than prior art surfactants, which exhibits excellent conditioning effects and fabric softening effects, and which can be widely used in a toiletry or detergent composition. Basic amino-acid derivatives or salts thereof obtained by reacting glycidyl ethers with basic amino acids or salts thereof are incorporated into a toiletry or detergent composition or a conditioning agent.

This application is a Divisional of application Ser. No. 08/796,741,filed on Feb. 6, 1997, now pending.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a surfactant. More specifically, thepresent invention relates to a novel surfactant which is less irritatingto the skin or the mucous membrane than prior art surfactants, whichexhibits excellent hair conditioning effects and fabric softeningeffects, and which can be widely used in a toiletry or detergentcomposition or the like.

2. Related Art

A surfactant that is less irritating to the skin or the mucous membranethan prior art surfactants is preferably used in a composition oftoiletries such as a face wash, a shampoo, a rinse, a hair conditioner,a body shampoo or the like and in a detergent composition. Further, hairtoiletries such as a rinse, a hair conditioner, a hair treatment and thelike are expected to have such conditioning effects that thesetoiletries make the hair smooth and suppress a dry and hard feeling.

Known examples of surfactants that are less irritating to the skin orthe mucous membrane include acylamino-acid derivatives such asN-acylglutamic acid salt, N-acylglycine salt, N-acylarginine ethyl estersalt and the like. But the above-mentioned acylamino-acid derivativesgive the hair low levels of conditioning effects, and these derivativesare, therefore, not satisfactory as conditioning agents such as a rinse,a hair conditioner and the like. Besides, with regard to the bubblingproperty, a further improvement thereof has been in demand.

As another surfactant of an amino-acid derivative type, a surfactantformed by adding a glycidyl ether to a neutral amino acid or an acidicamino acid is known. For example, N-(3-alkyl-2-hydroxypropyl)sarcosineand N,N-bis(3-alkyl-2-hydroxypropyl)glycine formed upon using sarcosineand glycine are described in E. Ulsperger, Fette, seifen, anstrichm., 68(11), 964-967 (1966). Further, N-(3-alkyl-2-hydroxypropyl)serine,N-(3-alkyl-2-hydroxypropyl)aspartic acid and the like are described inWO 94/21595. However, these neutral and acidic amino-acid derivativesgive the hair still unsatisfactory conditioning effects.

Furthermore, amino-acid derivatives formed by adding an 1,2-epoxyalkaneto an amino acid are described in Japanese Laid-Open Patent Application(Kokai) No. 22,417/1973. However, these amino-acid derivatives are notsaid to be satisfactory in terms of solubility.

Meanwhile, an alkyl quaternary ammonium salt and the like have beenwidely used as conditioning agents or fabric softening agents. It hasbeen known that these conditioning agents are electrically adsorbed onthe hair surface, which is weakly acidic, or the fabric surface, whichis negatively charged in the rinsing water, to impart a good combingproperty, a smoothness and the like to the hair. Nevertheless, theystrongly irritate the skin, the mucous membrane and the like, and areproblematic also in terms of biodegradability. Furthermore, they lowerthe hygroscopic property of fabric.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide a surfactant whichis less irritating to the skin, the mucous membrane and the like thanprior art surfactants, and which exhibits a high solubility and a highbubble stability as well as to provide a hair toiletry which exhibitsexcellent conditioning effects of imparting a smoothness to the hair andsuppressing a dry and hard feeling of the hair, and a fabric softenerwhich exhibits excellent softening effects and maintains the hygroscopicproperty of fabric.

Under these circumstances, the present inventors have assiduouslyconducted investigations, and have consequently found that basicamino-acid derivatives formed by reacting glycidyl ethers which areepoxy compounds with basic amino acids such as arginine, lysine and thelike exhibit excellent conditioning effects, excellent softeningeffects, a low level of irritation, an excellent solubility and anexcellent bubble stability. These findings have led to the completion ofthe present invention. The amino-acid derivatives of the presentinvention can widely be used in toiletry and detergent compositions, andare especially appropriate as hair toiletries such as a shampoo, arinse, a treatment and the like.

The surfactant of the present invention contains at least one type ofbasic amino-acid derivatives or salts thereof, wherein the derivativesare represented by formulas (1) to (4) ##STR1## wherein R¹ to R⁶ eachrepresent a linear or branched alkyl or alkenyl group having from 8 to22 carbon atoms, provided that R² and R³, or R⁵ and R⁶ are the same ordifferent, m represents an integer of from 1 to 5, and X represents anyof the following substituents, ##STR2##

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Salts of the basic amino-acid derivatives include inorganic salts suchas hydrochloride and a sulfate, and organic acid salts such as anacetate, a citrate, a p-toluenesulfonate, a fatty acid salt, an acidicamino-acid salt and an L- or DL-pyrrolidonecarboxylate.

These basic amino-acid derivatives or salts thereof may be used eithersingly or in combination.

The basic amino-acid derivatives of formulas (1) to (4) can be easilyproduced by conventional methods known to those of ordinary skill in theart such as by the same process of treating an amino acid with anepoxyalkane as described in Japanese Laid-Open Patent Application(Kokai) No. 22,417/1973, namely by reacting a basic amino acid with aglycidyl ether represented by formula (8) ##STR3## wherein R¹¹represents a linear or branched alkyl or alkenyl group having from 8 to22 carbon atoms under alkaline conditions in a lower alcohol or a mixedsolvent of a lower alcohol and water.

The above-mentioned glycidyl ether can be obtained by reacting, forexample, a natural or synthetic saturated or unsaturated higher alcoholwith epichlorohydrin. Examples thereof include decyglycidyl ether,dodecylglycidyl ether, tetradecylglycidyl ether and stearylglycidylether. These may be used either singly or in combination. Commerciallyavailable examples of the glycidyl ether include Epiol L-41(decyglycidyl ether) and Epiol SK (stearylglycidyl ether) made by NOFCorporation, Heloxy 8 (mixture of dodecylglycidyl ether andtetradecylglycidyl ether) made by ACI Japan, Ltd., Denacol EX-192(mixture of dodecylglycidyl ether and tetradecylglycidyl ether) made byNagase Chemicals, Ltd., and SY-25L (mixture of decylglycidyl anddodecylglycidyl ether) made by Sakamoto Yakuhin Kogyo Co., Ltd.

Examples of the basic amino acid include arginine, lysine, ornithine,histidine and hydroxylysine.

In the case of, for example, lysine and ornithine among the basic aminoacids, the moiety that binds to the glycidyl ether is considered to bepreferentially an ε-amino group (lysine) and an δ-amino group(ornithine). An α-amino group is also available. A compound obtained byreacting two molecules of the glycidyl ether with an ε-amino group, aδ-amino group or an α-amino group is also included therein. Further, acompound obtained by reacting one molecule of the glycidyl ether witheach of an ε-amino group (δ-amino group in ornithine) and α-amino group,and a compound obtained by adding three or four molecules of theglycidyl ether to one molecule of an amino acid may be used.

Amino-acid derivatives obtained by reacting a neutral or acidic aminoacid with a glycidyl ether are useful as a surfactant also. Examples ofthe neutral amino acids include glycine, alanine, β-alanine, sarcosine,N-methyl-β-alanine, valine, leucine, isoleucine, serine, threonine,methionine, phenylalanine, tyrosine, proline, hydroxyproline,homoserine, α-aminobutyric acid, α-aminovaleric acid, α-aminocaproicacid, phenylglycine, cystine, cysteine, 3,4-dihydroxyphenylalanine andγ-aminobutyric acid. Examples of the acidic amino acid include glutamicacid and aspartic acid. However, these neutral or acidic amino-acidderivatives cannot provide satisfactory conditioning effects andsoftening effects. Incidentally, these neutral or acidic amino acidderivatives may be contained unless the effect of the present inventionis impaired.

In the reaction between the glycidyl ether and the amino acid, it isadvisable to use the amino acid in the form of an alkali metal salt orto conduct the reaction under alkaline conditions in order to increasereactivity and prevent side reactions. However, with respect toarginine, the reaction could be conducted without using theseconditions.

As the reaction solvent, a lower alcohol such as methyl alcohol, ethylalcohol, n-propyl alcohol or i-propyl alcohol, or a mixed solvent ofthis lower alcohol and water is ordinarily used. The mixing ratio of thelower alcohol to water varies depending on the types of the amino acidand the glycidyl ether. It may be between 100:0 and 10:90, preferably1:1 to 2:1. When the amount of the alcohol is small, the solubility ofthe glycidyl ether is decreased, and the reaction rate is notablyreduced.

The reaction temperature varies depending on the type and thecomposition of the reaction solvent. It is generally between 70° C. and100° C., preferably between 80° C. and 95° C. It is advisable that thereaction be conducted under reflux. The glycidyl ether may be added at atime before heating, or in divided portions or dropwise continuouslyafter heating is started. In order to control formation of by-products,it is preferable to add the same dropwise continuously after heating isstarted.

The thus-obtained reaction product sometimes contains, besides thedesired amino-acid derivatives, by-products such as an unreacted aminoacid, a glycidyl ether hydrolyzate and the like. In this case,purification can be conducted by a known method such as extraction,recrystallization, chromatography or the like. The resulting product maybe used in the form of a mixture unless it influences a surfaceactivity.

When a higher alcohol is incorporated into the surfactant of the presentinvention, the hair conditioning effects can be further increased. Thatis, the present invention provides a toiletry or detergent compositioncomprising a surfactant of any of formulas (1) to (4) and a higheralcohol.

This higher alcohol is represented by the formula (9)

    R.sup.12 --OH                                              (9)

wherein R¹² represents a linear or branched alkyl or alkenyl grouphaving from 12 to 36 carbon atoms. Examples thereof which are widelyused include cetyl alcohol, stearyl alcohol, behenyl alcohol, isostearylalcohol, octyl dodecanol and olyl alcohol.

The higher alcohol and the surfactant in the above-mentioned detergentcomposition can be used at a relatively wide ratio. The weight ratio ofthe higher alcohol to the surfactant is preferably between 10:100 and100:0.5, more preferably between 50:100 to 100:5. When it is less than10:100, the effect provided by the higher alcohol is not sufficientlyexhibited. When it is more than 100:5, the conditioning effects arereduced.

The surfactant of the present invention can be incorporated intocompositions of toiletries and detergents, for example, hair careproducts such as a shampoo, a rinse and a treatment, toiletries such asa cleansing cream and a massage cream, a body cleaning agent such as abody shampoo, a sterile detergent, a fabric softener, a kitchendetergent and a cleaning detergent.

The amount of the surfactant in the composition of the present inventioncan be appropriately determined depending on the use and theformulation. It is generally between 0.1% by weight and 95% by weight.Another surfactant may be jointly used in such a composition unless itimpairs the effect of the present invention. Examples of the othersurfactant include anioinic surfactants such as a higher fatty acidsalt, a polyoxyalkyl ether sulfuric acid salt, an N-acylaminocarboxylicacid salt, a polyoxyethylene alkyl ether carboxylic acid salt, anN-acyltaurine salt and a sulfosuccinic acid surfactant, amphylyticsurfactants such as an alkyldimethylaminoacetic acid betaine, a higherfatty acid amide propyldimethylaminoacetic acid betaine and animidazoline surfactant; nonionic surfactants such as alkyl saccharidesurfactants, polyoxyethylene alkyl ether surfactants, higher fatty acidalkanolamide and amine oxide; and cationic surfactants such as analkyltrimethylammonium chloride and an N-acylarginine lower alkyl esterpyrrolidonecarboxylic acid salt.

In addition to the above-mentioned surfactants, a variety of additiveswhich are ordinarily used can be added. Examples thereof include wettingagents such as ethylene glycol, propylene glycol, 1,3-butylene glycol,glycerol and sorbitol; emulsifying agents such as glycerol monostearateand polyoxyethylene sorbitan monolaurate; hydrocarbons such as liquidparaffin, vaseline and squalane; esters such as isopropyl myristate andoctyldodecyl myristate; cellulose derivatives such as hydroxyethylcellulose, hydroxypropyl cellulose and carboxymethyl cellulose; anioinicpolymers such as an acrylic acid polymer; silicon derivatives; andcationic polymers such as cationic guar gum. Further, antibiotics suchas paraben derivatives, perfumes, pigments, viscosity modifiers,pearling agents, antioxidants, disinfectants, anti-inflammatory agents,UV absorbers, pH adjustors and crude drugs can be used as required.

EXAMPLES

The present invention is illustrated specifically by referring to thefollowing examples. However, the present invention is not limited tothese examples.

Example 1 N-(2-hydroxy-3-dodecyloxypropyl)-L-arginine hydrochloride

L-arginine (17.4 g, 0.1 mols) was dissolved in 100 ml of water in athree-necked round flask, and 100 ml of i-propanol were added thereto.Then, 24.2 g (0.1 mols) of dodecylglycidyl ether (made by SakamotoYakuhin Kogyo Co., Ltd.) were added dropwise thereto over a period of 30minutes while being heat-refluxed and stirred. Further, the mixture wasstirred under reflux for 3 hours. It was identified through TLC and gaschromatography that dodecylglycidyl ether disappeared. Thereafter, theresulting mixture was neutralized with 10.1 g (0.1 mols) of 36%hydrochloric acid. The reaction solution was concentrated under reducedpressure, and the residue was purified through silica-gel columnchromatography (Kieselgel 60 made by Merck & Co., Inc., eluent=mixtureof chloroform, methanol and acetic acid at a ratio of 3:1:0.5) to give15.0 g of N-(2-hydroxy-3-dodecyloxypropyl)-L-arginine hydrochloride(yield 36.0%).

TLC (mixture of butanol, acetic acid and water at a ratio of 4:1:2):Rf=0.64 ESI mass spectrum: 417.5 (MH+) IR (NaCl, cm⁻¹): 3177, 2955,2920, 2853, 1692, 1628, 1468, 1397, 1377, 1215, 1116

Example 2 N,N-bis(2-hydroxy-3-dodecyloxypropyl)-L-arginine hydrochloride

L-arganine (17.4 g, 0.1 mols) was dissolved in 100 ml of water in athree-necked round flask, and 100 ml of i-propanol were added thereto.Then, 48.4 g (0.2 mols) of dodecylglycidyl ether were added dropwisethereto over a period of 30 minutes while being heat-refluxed andstirred. Further, the mixture was stirred under reflux for 3 hours. Itwas identified through TLC and gas chromatography that dodecylglycidylether disappeared. Thereafter, the resulting mixture was neutralizedwith 10.1 g (0.1 mols) of 36% hydrochloric acid. The reaction solutionwas concentrated under reduced pressure, and the residue was purifiedthrough silica-gel column chromatography (Kieselgel 60, eluent=mixtureof chloroform, methanol and acetic acid at a ratio of 3:1:0.5) to give11.4 g of N,N-bis(2-hydroxy-3-dodecyloxypropyl)-L-arginine hydrochloride(yield 17.2%).

TLC (mixture of butanol, acetic acid and water at a ratio of 4:1:2):Rf=0.72 ESI mass spectrum: 659.77 (MH+) IR (NaCl, cm⁻¹): 3177, 2955,2920, 2853, 1692, 1628, 1468, 1397, 1377, 1215, 1120

Example 3 N-(2-hydroxy-3-octadecyloxypropyl)-L-arginine hydrochloride

L-arginine (17.4 g, 0.1 mols) was dissolved in 100 ml of water in athree-necked round flask, and 100 ml of i-propanol were added thereto.Then, 32.6 g (0.1 mols) of octadecylglycidyl ether (made by SakamotoYakuhin Kogyo Co., Ltd.) were added dropwise thereto over a period of 30minutes while being heat-refluxed and stirred. Further, the mixture wasstirred under reflux for 3 hours. It was identified through TLC and gaschromatography that octadecylglycidyl ether disappeared. Thereafter, theresulting mixture was neutralized with 10.1 g (0.1 mols) of 36%hydrochloric acid. The reaction solution was concentrated under reducedpressure, and the residue was purified through silica-gel columnchromatography (Kieselgel 60, eluent=mixture of chloroform, methanol andacetic acid at a ratio of 3:1:0.5) to give 21.2 g ofN-(2-hydroxy-3-octadecyloxypropyl)-L-arginine hydrochloride (yield42.3%).

TLC (mixture of butanol, acetic acid and water at a ratio of 4:1:2):Rf=0.64 ESI mass spectrum: 501.5 (MH+) IR (NaCl, cm⁻¹): 3175, 2955,2917, 2851, 1692, 1628, 1468, 1377, 1215, 1121

Example 4 N,N-bis(2-hydroxy-3-octadecyloxypropyl)-L-argininehydrochloride

L-arginine (17.4 g, 0.1 mols) was dissolved in 100 ml of water in athree-necked round flask, and 100 ml of i-propanol were added thereto.Then, 65.2 g (0.2 mols) of octadecylglycidyl ether were added dropwisethereto over a period of 30 minutes while being heat-refluxed andstirred. Further, the mixture was stirred under reflux for 3 hours. Itwas identified through TLC and gas chromatography that octadecylglycidylether disappeared. Thereafter, the resulting mixture was neutralizedwith 10.1 g (0.1 mols) of 36% hydrochloric acid. The reaction solutionwas concentrated under reduced pressure, and the residue was purifiedthrough silica-gel column chromatography (Kieselgel 60, eluent=mixtureof chloroform, methanol and acetic acid at a ratio of 3:1:0.5) to give10.2 g of N,N-bis(2-hydroxy-3-octadecyloxypropyl)-L-argininehydrochloride (yield 12.3%).

TLC (mixture of butanol, acetic acid and water at a ratio of 4:1:2):Rf=0.72 ESI mass spectrum: 827.7 (MH+) IR (NaCl, cm⁻¹): 3175, 2955,2917, 2851, 1692, 1628, 1468, 1377, 1215, 1121

Example 5 Nε-(2-hydroxy-3-dodecyloxypropyl)-L-lysine hydrochloride

L-lysine hydrochloride (18.3 g, 0.1 mols) and 2.0 g (0.2 mols) of sodiumhydroxide were dissolved in 100 ml of water in a three-necked roundflask, and 100 ml of i-propanol were added thereto. Then, 24.2 g (0.1mols) of dodecylglycidyl ether were added dropwise thereto over a periodof 30 minutes while being heat-refluxed and stirred. Further, themixture was stirred under reflux for 3 hours. It was identified throughTLC and gas chromatography that dodecylglycidyl ether disappeared.Thereafter, the resulting mixture was neutralized with 10.1 g (0.1 mols)of 36% hydrochloric acid. The reaction solution was concentrated underreduced pressure, and the residue was purified through silica-gel columnchromatography (Kieselgel 60, eluent=mixture of chloroform, methanol andacetic acid at a ratio of 3:1:0.5) to give 10.1 g ofNε-(2-hydroxy-3-dodecyloxypropyl)-L-lysine hydrochloride (yield 23.7%).

TLC (mixture of butanol, acetic acid and water at a ratio of 4:1:2):Rf=0.42 ESI mass spectrum: 389.4 (MH+) IR (NaCl, cm⁻¹): 2955, 2923,2853, 1620, 1586, 1468, 1120

Example 6

L-lysine hydrochloride (18.3 g, 0.1 mols) and 2.0 g (0.2 mols) of sodiumhydroxide were dissolved in 100 ml of water in a three-necked roundflask, and 100 ml of i-propanol were added thereto. Then, 48.4 g (0.2mols) of dodecylglycidyl ether were added dropwise thereto over a periodof 30 minutes while being heat-refluxed ana stirred. Further, themixture was stirred under reflux for 3 hours. It was identified throughTLC and gas chromatography that dodecylglycidyl ether disappeared.Thereafter, the resulting mixture was neutralized with 10.1 g (0.1 mols)of 36% hydrochloric acid. The reaction solution was concentrated underreduced pressure, and the residue was purified through silica-gel columnchromatography (Kieselgel 60, eluent=mixture of chloroform, methanol andacetic acid at a ratio of 3:1:0.5) to give 30.7 g of hydrochloride of anadduct of dodecylglycidyl ether and L-lysine at a ratio of 2:1 (yield46.1%).

ESI mass spectrum: 631.6 (MH+) IR (NaCl, cm⁻¹): 2955, 2923, 2853, 1619,1574, 1468, 1410, 1122

Example 7 Nε-(2-hydroxy-3-octadecyloxypropyl)-L-lysine hydrochloride

L-lysine hydrochloride (18.3 g, 0.1 mols) and 2.0 g (0.2 mols) of sodiumhydroxide were dissolved in 100 ml of water in a three-necked roundflask, and 100 ml of i-propanol were added thereto. Then, 32.6 g (0.1mols) of octadecylglycidyl ether were added dropwise thereto over aperiod of 30 minutes while being heat-refluxed and stirred. Further, themixture was stirred under reflux for 3 hours. It was identified throughTLC and gas chromatography that octadecylglycidyl ether disappeared.Thereafter, the resulting mixture was neutralized with 10.1 g (0.1 mols)of 36% hydrochloric acid. The reaction solution was concentrated underreduced pressure, and the residue was purified through silica-gel columnchromatography (Kieselgel 60, eluent=mixture of chloroform, methanol andacetic acid at a ratio of 3:1:0.5) to give 12.0 g ofNε-(2-hydroxy-3-octadecyloxypropyl)-L-lysine hydrochloride (yield23.6%).

TLC (mixture of butanol, acetic acid and water at a ratio of 4:1:2):Rf=0.42 ESI mass spectrum: 473.5 (MH+) IR (NaCl, cm⁻¹): 2955, 2923,2853, 1620, 1586, 1468, 1120

Example 8

L-lysine hydrochloride (18.3 g, 0.1 mols) and 2.0 g (0.2 mols) of sodiumhydroxide were dissolved in 100 ml of water in a three-necked roundflask, and 100 ml of i-propanol were added thereto. Then, 65.2 g (0.2mols) of octadecylglycidyl ether were added dropwise thereto over aperiod of 30 minutes while being heat-refluxed and stirred. Further, themixture was stirred under reflux for 3 hours. It was identified throughTLC and gas chromatography that octadecylglycidyl ether disappeared.Thereafter, the resulting mixture was neutralized with 10.1 g (0.1 mols)of 36% hydrochloric acid. The reaction solution was concentrated underreduced pressure, and the residue was purified through silica-gel columnchromatography (Kieselgel 60, eluent=mixture of chloroform, methanol andacetic acid at a ratio of 3:1:0.5) to give 40.3 g of hydrochloride of anadduct of octadecylglycidyl ether and L-lysine at a ratio of 2:1 (yield48.3%).

ESI mass spectrum: 799.7 (MH+) IR (NaCl, cm⁻¹): 2955, 2923, 2853, 1619,1574, 1468,1410, 1122

Example 9

L-arginine was reacted with dodecylglycidyl ether in the same manner asin Example 1. After it was identified through TLC and gas chromatographythat dodecylglycidyl ether disappeared, the reaction solution wasneutralized with 36% hydrochloric acid. The reaction solution wasconcentrated under reduced pressure to give 47.3 g of a reactionmixture.

Example 10

L-lysine was reacted with dodecylglycidyl ether in the same manner as inExample 5. After it was identified through TLC and gas chromatographythat dodecylglycidyl ether disappeared, the reaction solution wasneutralized with 36% hydrochloric acid. The reaction solution wasconcentrated under reduced pressure to give 52.1 g of a reactionmixture.

Example 11

L-arginine (17.4 g, 0.1 mols) was dissolved in 100 ml of water in athree-necked round flask, and 100 ml of i-propanol were added thereto.Then, 25.6 g (0.1 mols) of Heroxine 8 (made by ACI Japan Ltd.) wereadded dropwise thereto over a period of 30 minutes while beingheat-refluxed and stirred. Further, the mixture was stirred under refluxfor 3 hours. After it was identified through TLC and gas chromatographythat glycidyl ether disappeared, 12.9 g (0.1 mols) ofDL-pyrrolidonecarboxylic acid were added thereto. Then, i-propyl alcoholwas distilled off under reduced pressure, and the reaction solution waspoured into cold acetone to give 50.9 g of a mixture ofN-(2-hydroxy-3-dodecyloxy)propyl-L-arginine.DL-pyrrolidonecarboxylicacid salt and N-(2-hydroxy-3-tetradecyloxy)propyl-L-arginine.DL-pyrrolidonecarboxylic acid salt. The ESI massspectrum of the resulting mixture was measured, and peaks of 417.5 (MH+)and 445.5 (MH+) were identified.

Example 12

With respect to the surfactants obtained in Examples 1 and 5 andtrimethylstearylammonium chloride and N-cocoyl-L-arginine ethylester.DL-pyrrolidonecarboxylic acid salt as comparative examples, theprimary irritations of the skin and the eye mucous membrane weremeasured by the following test methods. The results are shown in Table1.

(1) Test for Primary Skin Irritation

Each of four New Zealand white male rabbits was seal-coated with a patchtest plaster permeated with 0.3 ml of a 1% surfactant aqueous solution,and was allowed to stand for 24 hours. Then, the plaster was removedfrom the rabbit. After 24 hours, the irritation was evaluated accordingto the following Draise's evaluation standard.

    ______________________________________    Draise's evaluation score                     Irritation level    ______________________________________    4 or more        heavy    from 2 to less than 4                     light    less than 2      slight    ______________________________________

(2) Test for Primary Eye Mucous Membrane Irritation

The lower eyelids of both eyes of each of four New Zealand white malerabbits were formed into a bag shape, and 0.1 ml of a 1% surfactantaqueous solution were dropped therein. Thereafter, the upper and lowereyelids were gently joined. The irritation was evaluated according tothe following Draise's evaluation standard 24 hours after addition ofthe drops.

    ______________________________________    Draise's evaluation score                     Irritation level    ______________________________________    50 or more       heavy    from 20 to less than 50                     medium    from 10 to less than 20                     light    less than 10     slight    ______________________________________

                  TABLE 1    ______________________________________                        Irritation                               Mucous                        Skin   membrane    ______________________________________    Examples Compound in Example 1                              slight   slight             Compound in Example 5                              slight   slight    Comparative             trimethylstearylammonium                              heavy    medium    Examples chloride             Nα-cocoyl-L-arginine                              slight   slight             ethyl ester salt    ______________________________________

From Table 1, it becomes apparent that the surfactant of the presentinvention gives a low level of irritation.

Example 13

The surfactants were measured for the bubbling power and the bubblestability by the following test methods.

Tests for bubbling power and bubble stability:

Each of the surfactants was adjusted with purified water such that theconcentration of the activator reached 0.25% by weight. Fifty grams ofthe aqueous solution were charged into a 350-milliliter home mixer, andstirred for 5 seconds. The volume (ml) of the bubbles immediately afterthe stirring and the volume (ml) of the bubbles after 5 minutes of thestirring were measured. The volume of bubbles immediately after thestirring was defined as a bubbling power, and the bubble retentioncalculated from the following equation was defined as a bubblestability.

Bubble retention (%)=(volume of bubbles after 5 minutes ofstirring/volume of bubbles immediately after stirring)×100

                  TABLE 2    ______________________________________                                 Bubble                         Bubbling                                 stability                         power (ml)                                 (%)    ______________________________________    Examples            Compound in Example 1                               150       80.0            Compound in Example 5                               130       69.2    Comparative            N-(2-hydroxy-3-    80        37.5    Examples            dodecyloxypropyl)methyltaurine            sodium salt            N-(2-hydroxy-3-dodecyloxypropyl)                               120       58.3            sarcosine sodium salt            Coconut oil fatty acid amide propyl                               140       64.3            betaine solution            N-coconut oil fatty acid-L-glutamic                               130       61.5            acid triethanolamine    ______________________________________

From Table 2, it becomes apparent that the surfactant of the presentinvention exhibits the bubbling power which is the same as, or higherthan, that of the usual surfactant which exhibits a low level ofirritation.

Example 14

The solubility of each surfactant in water was tested by the followingmethod.

Each of the surfactants was diluted with water to a concentration of 1,3, 5, 10 or 20% by weight, and the solution was rendered uniform whilebeing stirred at 50° C. The resulting solution was allowed to standovernight at 25° C., and the solubility was then visually measured. Theresults are shown in Table 3.

                  TABLE 3    ______________________________________                1%    3%      5%      10%  20%    ______________________________________    Invention           Compound in                      clear   clear clear clear                                               clear           Example 1    Compara-           N-(2-hydroxy-                      slightly                              turbid                                    milk- milk-                                               milk-    tive   hexadecyl)-L-                      turbid        white white                                               white    Example           arginine           hydrochloride    ______________________________________

From Table 3, it becomes apparent that the compound of the presentinvention exhibits a higher solubility in water. Accordingly, a toiletryor detergent composition having a higher solution stability can beformed therefrom because separation or precipitation of the surfactantcomponent can be prevented effectively.

Example 15

A 0.5% surfactant aqueous solution (150 g) was prepared. A hairpiecemade of 20 g of the healthy hair of a Japanese woman was washed with a1% lauryl ether sodium sulfate aqueous solution, and then dipped in theabove-mentioned aqueous solution for 1 minute. The resulting hairpiecewas gently rinsed with running hot water, and then dried using a dryer.With respect to softness, combing property, moist feeling and stickyfeeling of the hair after drying, the organoleptic evaluation wasconducted by 8 expert panelists. In the evaluation, average values werecalculated on the basis of the following standard. When the averagevalue was 4.5 or more, the property was evaluated as very good (⊚). Whenthe average value was between 3.5 and 4.4, the property was evaluated asgood (◯). When the average value was between 2.5 and 3.4, the propertywas evaluated as common (.increment.). When the average value was 2.4 orless, the property was evaluated as bad.

<Evaluation standard>

Softness of the hair:

5: very soft and smooth

4: soft

3: common

2: slightly hard

1: hard

Combing property of the hair:

5: Combing is conducted well and quite smoothly.

4: Combing is conducted well.

3: Combing property is common.

2: Combing property is slightly bad.

1: Combing property is bad, and combing is sometimes interrupted.

Moist feeling:

5: quite moist

4: moist

3: common

2: slightly dry and hard

1: quite dry and hard

Sticky feeling:

5: not sticky

4: little sticky

3: common

2: slightly sticky

1: sticky

                  TABLE 4    ______________________________________                      Comparative                      Example            Example   (N-(2-hydroxyhexa-            Compound in                      decyl)-L-arginine            Example 1 hydrochloride                                   Untreated    ______________________________________    Softness  ⊚                          ∘                                       bad    Combing property              ∘                          Δ      bad    Moist feeling              ⊚                          ∘                                       bad    Sticky feeling              ∘                          ∘                                       bad    ______________________________________

Example 16

A detergent composition shown in Table 5 was prepared. Each of eightexpert panelists washed the hair with a commercially available shampoo,and then used the detergent composition. With respect to a softness, acombing property, a moist feeling and a sticky feeling of the hair afterdrying, the organoleptic evaluation was conducted by them. In theevaluation, average values were calculated on the basis of the followingstandard. When the average value was 4.5 or more, the property wasevaluated as very good (⊚). When the average value was between 3.5 and4.4, the property was evaluated as good (◯). When the average value wasbetween 2.5 and 3.4, the property was evaluated as common (.increment.).When the average value was 2.4 or less, the property was evaluated asbad (X).

<Evaluation standard>

Softness of the hair:

5: very soft and smooth

4: soft

3: common

2: slightly hard

1: hard

Combing property of the hair:

5: Combing is conducted well and quite smoothly.

4: Combing is conducted well.

3: Combing property is common.

2: Combing property is slightly bad.

1: Combing property is bad, and combing is sometimes interrupted.

Moist feeling:

5: quite moist

4: moist

3: common

2: slightly dry and hard

1: quite dry and hard

Sticky feeling:

5: not sticky

4: little sticky

3: common

2: slightly sticky

1: sticky

                                      TABLE 5    __________________________________________________________________________                    Examples      Comparative Examples    __________________________________________________________________________    Surfactant in Production Example 1                    1.0    Surfactant in Production Example 2                      1.0    Surfactant in Production Example 3                        1.0    Surfactant in Production Example 5                          1.0    Surfactant in Production Example 8                            1.0    Surfactant in Production Example 10                              1.0    Surfactant in Production Example 11                                1.0    N-(2-hydroxy-3-               1.0    dodecyloxypropyl)serine    N-(2-hydroxy-3-                 1.0    dodecyloxypropyl)methyltaurine    N-(2-hydroxy-3-                   1.0    dodecyloxypropyl)sarcosine    Trimethylstearylammonium chloride   1.0    Dimethyldistearylammonium chloride    1.0    Nα-cocoyl-L-arginine ethyl ester  1.0    Cetanol         3.0                      3.0                        3.0                          3.0                            3.0                              3.0                                3.0                                  3.0                                    3.0                                      3.0                                        3.0                                          3.0                                            3.0    Propylene glycol                    1.0                      1.0                        1.0                          1.0                            1.0                              1.0                                1.0                                  1.0                                    1.0                                      1.0                                        1.0                                          1.0                                            1.0    Purified water  * * * * * * * * * * * * *    ORGANOPEPTIC    EALUATION    Softness        ⊚                      ⊚                        ⊚                          ⊚                            ∘                              ⊚                                ⊚                                  x x x ⊚                                          ∘                                            Δ    Combing property                    ∘                      ⊚                        ∘                          ∘                            ∘                              ∘                                ∘                                  x x x ∘                                          ∘                                            Δ    Moist feeling   ⊚                      ⊚                        ⊚                          ∘                            ∘                              ⊚                                ∘                                  x x x Δ                                          ∘                                            ⊚    Sticky feeling  ∘                      Δ                        ∘                          ∘                            Δ                              ∘                                ∘                                  x x x ∘                                          Δ                                            x    __________________________________________________________________________     *balance

From Tables 4 and 5, it becomes apparent that the surfactant and thedetergent composition of the present invention exhibit excellentconditioning effects.

Example 17 Shampoo

A composition shown in each of Tables 6 and 7 was heat-dissolved at from70 to 80° C., and then cooled to room temperature to obtain a shampoo.This shampoo exhibited an excellent rinsing property, and feeling aftercleaning was satisfactory.

                  TABLE 6    ______________________________________    Composition                  Amount    ______________________________________    Compound in Example 1        5.0    N-cocoyl-L-glutamic acid TEA 2    Polyoxyethylene (3) lauryl ether sodium sulfate                                 10    Lauric acid monoethanolamide 1    Propylene glycol             5    Cationic polymer ("MERQUAT 100" made by MERCK & Co.,                                 0.3    Inc.)    Antiseptic                   0.1    Perfume                      0.1    EDTA sodium salt             0.1    Purified water               balance    ______________________________________

                  TABLE 7    ______________________________________    Composition                 Amount    ______________________________________    Compound in Example 5       1.0    Lauric acid amide propylbetaine                                15    Coconut oil fatty acid diethanolamide                                5    DL-pyrrolidonecarboxylic acid sodium salt                                5    Ampholytic polymer ("PLAS SIZE L-401" made by GOO                                0.8    Chemical Co., Ltd.)    Citric acid    Antiseptic                  0.5    Perfume                     0.1    Purified water              0.1                                balance    ______________________________________

Example 18 Rinse

A composition shown in each of Tables 8 to 10 was heat-dissolved at from70 to 80° C., and then cooled to room temperature to obtain a rinse.This rinse exhibited an excellent rinsing property, and feeling afterdrying was satisfactory.

                  TABLE 8    ______________________________________    Composition                Amount    ______________________________________    Compound in Example 11     5    Polyoxyethylene (3) sulfosuccinic acid sodium salt                               5    Cocoylisethionic acid sodium salt                               2    Pyroglutamic acid glyceryl oleate                               1    N-lauroyl-β-alanine TEA                               1    Polyethylene glycol monostearate                               0.5    Emorient oil ("Eldew CL-301" made by Ajinomoto Co.,                               3    Inc.)    Wetting agent ("Prodew 100" made by Ajinomoto Co.,                               5    Inc.)    Antiseptic                 0.1    Perfume                    0.1    Purified water             balance    ______________________________________

                  TABLE 9    ______________________________________    Compound              Amount    ______________________________________    Compound in Example 3 1    Isostearic acid diethanolamide                          2    Cetanol               2    Liquid paraffin       1    Polyoxyethylene (5) oleyl ether                          0.3    1,3-butylene glycol   5    Trimethylstearylammonium chloride                          0.1    Hydroxyethyl cellulose                          0.5    Antiseptic            0.1    Perfume               0.1    Purified water        balance    ______________________________________

                  TABLE 10    ______________________________________    Composition             Amount    ______________________________________    Compound in Example 5   6    Cetanol                 6    Glycerol                3    Partially deacetylated chitin                            0.5    Polyoxyethylene (20) sorbitan monostearate                            0.2    Antiseptic              0.1    N-laurolyllysine        trace    Purified water          balance    ______________________________________

Example 19 Hair Conditioner

A composition shown in each of Tables 11 and 12 was heat-dissolved atfrom 70 to 80° C., and then cooled to room temperature to obtain a hairconditioner.

                  TABLE 11    ______________________________________    Composition           Amount    ______________________________________    Compound in Example 2 1    Cetanol               5    Coconut oil fatty acid diethanolamide                          4    Dimethylpolysiloxane (1,000 cs)                          1    Polyethylene glycol (400)                          0.2    vaseline              0.5    Self-emulsifiable glycerol monostearate                          0.2    Glycerol              1    Hydroxyethyl cellulose                          0.8    Antiseptic            0.2    Purified water        balance    ______________________________________

                  TABLE 12    ______________________________________    Composition         Amount    ______________________________________    Compound in Example 6                        5    Behenyl alcohol     7    Isopropyl myristate 1    Dipropylene glycol  3    Polyoxyethylene (4) stearyl ether                        5    Polyethylene glycol dioleate                        0.5    Polyethylene glycol 0.5    Sodium lactate      0.1    Antiseptic          0.1    Purified water      balance    ______________________________________

Example 20 Hair Lotion

A composition shown in Table 13 was heat-dissolved at from 40 to 50° C.,and then cooled to room temperature to obtain a hair lotion.

                  TABLE 13    ______________________________________    Compound             Amount    ______________________________________    Compound in Example 5                         0.05    Oleyl alcohol        0.2    Liquid paraffin      0.5    Ethanol              5    Sorbitol             4    Polyoxyethylene (20) lauryl ether                         2.5    sorbitan monolaurate 0.5    Pigment              0.1    Perfume              0.1    Antiseptic           0.1    Purified water       balance    ______________________________________

Example 21

A commercially available cotton towel and an acryl jersey were washedtwice with a commercially available clothing detergent using an electricwashing machine (a double-tank type). Thereafter, the towel and jerseyrinsed with city water of ordinary temperature. Each of the surfactantswere adjusted with city water at a temperature of 25° C. such that theconcentration of the surfactant reached 50 ppm and a homogeneoussolution was obtained. The cotton towel and acryl jersey, which haveequal weights, soaked in the surfactant solution having a weight 30times greater than the combined weight of the cotton towel and acryljersey. After 3 minutes, the towel and jersey were dehydrated using theelectric washing machine. Thereafter, they were dried at a temperatureof 25° C. and a relative humidity of 40% for 24 hours, and thereafterevaluated.

(1) Test for Fabric Softness

With respect to softness, the organoleptic evaluation was conducted byeight panelists. In the evaluation, average values were calculated onthe basis of the following standard.

<Evaluation standard>

4: equal to distearyl dimethyl ammonium chloride

3: softer than trimethyl stearyl ammonium chloride

2: equal to trimethyl stearyl ammonium chloride

1: equal to untreated

(2) Test for Hygroscopic Property

According to JIS (Japan Industrial Standard) L 1096, a cotton toweltreated with each of the surfactants was cut into a rectangular fragment(20 mm×150 mm), and the end part of the fragment (5 mm) were soaked inthe water colored by blue dye. After five minutes, the height ofascended water was measured.

                  TABLE 14    ______________________________________                            Soft-  Hygroscopic    Surfactant              ness   (mm)    ______________________________________    Comparative            Distearyl dimethyl ammonium                                4      25    Example chloride    Example Trimethyl stearyl ammonium chloride                                2      37            Surfactant in Example 11                                4      77            Surfactant in Example 7                                4      80            Surfactant in Example 8                                4      77            Surfactant in Example 10                                3      77    ______________________________________

Example 22 Fabric Softener

A composition shown in each of Tables 15 and 16 was heat-dissolved atfrom 70 to 80° C., and then cooled to room temperature to obtain afabric softener. This fabric softener exhibited an excellent softeningproperty, and the hygroscopic property of fabric treated with it wassatisfactory.

                  TABLE 15    ______________________________________    Composition        Amount    ______________________________________    Compound in Example 11                       15.0    Glyceryl monostearate                       7.5    Stearic acid       1.0    Sodium chloride    0.2    Glycerol           2.0    Ethanol            5.0    Polyethylene glycol                       2.5    400                0.1    Pigment            0.1    Perfume            0.1    Antiseptic         balance    Purified water    ______________________________________

                  TABLE 16    ______________________________________    Composition       Amount    ______________________________________    Compound in Example 8                      7.5    Sorbitan monostearate                      7.5    Stearic acid      0.5    Sodium chloride   0.2    Ethylene glycol   5.0    Polyethylene glycol 400                      1.0    Pigment           0.1    Perfume           0.1    Antiseptic        0.1    Purified water    balance    ______________________________________

Obviously, numerous modifications and variations of the presentinvention are possible in light of the above teachings. It is thereforeto be understood that within the scope of the appended claims, theinvention may be practiced otherwise than as specifically describedherein.

This application is based on Japanese Patent Application No. 20126/1996filed with the Japanese Patent Office on Feb. 6, 1996, the entirecontents of which are herein incorporated by reference.

What is claimed as new and desired to be secured by Letters Patent ofthe United States is:
 1. A surfactant comprising a basic amino-acidderivative or a salt thereof, wherein the surfactant is obtained byheat-reacting a basic amino acid or a salt thereof with a glycidyl etherin an alcohol or in a mixed solvent of an alcohol and water,wherein saidbasic amino acid is selected from the group consisting of arginine,lysine, ornithine, histidine, hydroxylysine and mixtures thereof, andwherein said glycidyl ether has a linear or branched alkyl or alkenylgroup having from 8-22 carbon atoms.
 2. The surfactant of claim 1,wherein said glycidyl ether is selected from the group consisting ofdecylglycidyl ether, stearylglycidyl ether, dodecylglycidyl ether,tetradecylglycidyl ether and a mixture thereof.
 3. The surfactant ofclaim 1, wherein said salt of the basic amino acid is an alkali metalsalt.
 4. The surfactant of claim 1, wherein said alcohol is a loweralcohol.
 5. The surfactant of claim 1, wherein said alcohol is selectedfrom the group consisting of methyl alcohol, ethyl alcohol, n-propylalcohol, i-propyl alcohol and a mixture thereof.
 6. The surfactant ofclaim 1, wherein a mixing ratio of said alcohol to water in said mixedsolvent is between 100:0 and 10:90.
 7. The surfactant of claim 1,wherein a mixing ratio of said alcohol to water in said mixed solvent isbetween 1:1 and 2:1.
 8. The surfactant of claim 1, wherein saidheat-reacting step is conducted at a temperature between 80° C. and 95°C.
 9. The surfactant of claim 1, wherein said heat-reacting step isconducted under alkaline conditions.
 10. The surfactant of claim 1,wherein said basic amino acid is arginine.
 11. The surfactant of claim1, wherein said basic amino acid is lysine.
 12. The surfactant of claim1, wherein said basic amino acid is ornithine.
 13. The surfactant ofclaim 1, wherein said basic amino acid is histidine.
 14. The surfactantof claim 1, wherein said basic amino acid is hydroxylysine.
 15. Thesurfactant of claim 1, wherein said basic amino acid is said mixturethereof.
 16. A fabric softener composition comprising said surfactant ofclaim 1 or a salt thereof.